Dialkyl (phenylenedioxy)diacetates such as dimethyl (1,3-phenylenedioxy)diacetate are useful for producing polymers with high gas barrier properties useful in food packaging (e.g., see U.S. Pat. No. 4,435,590, incorporated herein by reference in its entirety).
U.S. Pat. No. 4,435,590 teaches preparation of a dimethyl phenylene-bis-oxyacetate derivative by reaction of hydroquinone with chloroacetic acid in the presence of aqueous NaOH to give the diacid which is then esterified. This procedure produces a substantial amount of trifunctional impurities which must be removed for most polymer applications. Such trifunctional impurities are difficult to remove and the overall yield of desired product achieved is in the 50% range.
It would be highly desirable to have a process for production of dialkyl (phenylenedioxy)diacetates in high yield.